Two week itinerary from Milan to Rome

do you think we can include Amalfi/Atrani or would it be a stretch?

Car rental or public transport

That would be a stretch. Your will be moving four times before heading for Amsterdam. Each of those moves will consume at least a half a day each. If you take time from the other locations, you will, in my opinion, short change those locations.

Definitely public transport. Between the ZTLs, speed cameras, and not being able to watch the scenery, driving in Italy can be a real pain.

The more the daughters are involved in the planning, the better the trip will be for everyone.

Just my opinion, others will probably differ.

Remove a day from the Cinque Terre and add it to Lake Como, Florence or Rome. We have been to Lake Como four times for up to two weeks, love it there.
Although we almost always rent cars in Europe, this itinerary would work better by trains.
Don’t add places south of Rome on this trip. Save them for a southern Italy focused trip.
A surprise at the end of your trip is a flight to Amsterdam yet you aren’t spending any time there. I encourage you to give some time to Amsterdam unless you have already been there. Amsterdam and Leiden are favorites of mine for a visit.

Too much time in CT, not enough time in Rome.

Yes, add more time in rome!

Did you accidentally cut off the end of the itinerary? How many days in Amsterdam? Why are you going there on your trip to Italy? Do you live there?

Most people (well, LOTS of people) pick Venice, Florence, Rome for their first trip to Italy. Do you really think your daughters will never be in Italy again? Have any of you been to Europe before? I ask that question because you may not understand how much time it takes to move from one place to the next one. I would also suggest that it is quite late to book some of these places for 2024. I specifically mean CT, the lake district, and possible Amalfi Coast (AC). Venice is always hard to book, but why aren't you going there? You'll have to take your fifth choice of hotel in Rome anyway. Are you aware you have to pre-book places like The Vatican, The Coliseum, and the Uffizi Gallery?

Regarding first trip to Europe, you need to buy (or go to the public library) for "Rick Steves Italy." Read every word in it. You have to think about whether you are going to book your hotels directly, or use the deceptive ease of Vinnie's Travel Site, where you won't be able to change anything without Vinnie's phone queue and approval. After 30 years of travel, I always book hotels directly. But it's time consuming, especially if you want to research discounts. (Not as common in high season, anyway.)

Five nights in Rome are not too many for a first visit. I've been back to Rome several times (sometimes on the way to somewhere else, but we stay a few nights) and have not exhausted the city and daytrips yet.

I wonder if the daughters chose CT, and for "the beach"? Do they ever get to a beach at home? The US has better beaches than Italy. Do they like forest hiking? That's why you go to CT. We didn't visit Milan until our third trip to Italy.

Thank you! Yes, the girls are definitely planning with me! It's just getting the itinerary right so we can do it as seamless as possible without wasting time.
We are spending 4 days in Amsterdam (our second time there) to go and see Taylor Swift... the reason for this trip...

It's actually not our first time in Italy. We've been to Venice with the girls. My husband and I have been to Rome, Naples, Capri, Sicily.

We've been to Venice with the girls.

That being the case, opt for Florence. And consider taking a day from the CT and adding it to Rome. Two full days and part of the arrival day just wont do justice to Rome.

Just checking on your itinerary between places - You arrive on the 19th, which will be very tiring, sorry see you're arriving from South Africa, less jet lag! So you have 1.5 days in Milan before traveling to LC. It may seem like you have more time than you really do, I would suggest each time you move hotels it takes part of a day, plus travel between places & getting settled into a new place.

20th: Day 2 - Milan
21st: Day 3 - Milan - Leave to Como?

22nd: Day 4 - Lake Como
23rd: Day 5 - Lake Como - Leave to CT?

24th: Day 6 - Cinque Terre
25th: Day 7 - Cinque Terre
26th: Day 8 - Cinque Terre
Leave to Florence?

27th: Day 9 - Florence
28th: Day 10 - Florence
29th: Day 11 - Florence - Leave to Rome?

30th: Day 12 - Rome
1st: Day 13 - Rome
2nd: Rome

Personally, I would skip CT & divide those days up between Lake Como, Florence & Rome, which all deserve much more time. CT will be jammed in June & staying in fewer places makes for a more relaxed, fun time especially with teens. Absolutely agreed no need to rent a car, trains work very well in Italy. Hope that's helpful.

Thank you for filling in your home area, on your profile.

The reason I asked if the teens were in on the planning is that I would like to know that they put as much study, internet research, and thought ... into their recommendations as you do. They would not be the first teens to pick CT out of a hat, because they get to wear bathing suits and go swimming. But that's a poor reason to drive the width of Italy to a place with narrow, crowded beaches, when you could be seeing art and architecture that is available nowhere else!

I have not been to Lake Como, but it is highly desirable in the summer, and is hard to book, either luxury level or bargain. That's why we haven't been there yet!

Thank you for all your insightful replies. Much appreciated!